Triethylamine → HCID 59750101, compound

HRID 499624Notes

Reaction equation

HRID 499624 reaction equation
[C:1]([C:3]1[CH:8]=[C:7]([N:9]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:10]2=[O:22])[CH:6]=[CH:5][N:4]=1)#[N:2].[C:23](OC)(=[O:31])[C:24]1[C:25](=[CH:27][CH:28]=[CH:29][CH:30]=1)[SH:26].C(N(CC)CC)C>C1(C)C=CC=CC=1>[O:22]=[C:10]1[N:9]([C:7]2[CH:6]=[CH:5][N:4]=[C:3]([C:1]3[S:26][C:25]4[CH:27]=[CH:28][CH:29]=[CH:30][C:24]=4[C:23](=[O:31])[N:2]=3)[CH:8]=2)[CH2:13][CH2:12][N:11]1[CH2:14][C:15]([O:17][C:18]([CH3:19])([CH3:21])[CH3:20])=[O:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 70859979HCID 70859979, compound

Product 1

HCID 59750101HCID 59750101, compoundYield 59.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

tert-Butyl [3-(2-cyano-4-pyridyl)-2-oxo-1-imidazolidinyl]acetate (0.80 g, 2.6 mmol) and methyl thiosalicylate (1.33 g, 7.8 mmol) were dissolved in toluene (6 ml), and triethylamine (2.0 ml, 14.3 mmol) was added thereto. The mixture was refluxed for 8 hrs. The solvent was evaporated, and the residue was subjected to a silica gel column chromatography. The fractions eluted with ethyl acetate-hexane (3:1, v/v) were collected, concentrated and recrystallized from tetrahydrofuran-hexane to give the titled compound (0.68 g, 58%).

Workup

  1. temperatureThe mixture was refluxed for 8 hrs
  2. customThe solvent was evaporated
  3. washThe fractions eluted with ethyl acetate-hexane (3:1
  4. customv/v) were collected
  5. concentrationconcentrated
  6. customrecrystallized from tetrahydrofuran-hexane

Sources & evidence

ORD record
ord-fb0e8fac36f34cc294c3d4dd8bec222d
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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